Synthesis, Molecular Docking and Biological Properties of Novel Thiazolo [4,5-b] pyridine Derivatives

被引:9
|
作者
Chaban, Taras, I [1 ]
Matiichuk, Yulia E. [1 ]
Shyyka, Olga Ya [2 ]
Chaban, Ihor G. [3 ]
Ogurtsov, Volodymyr V. [1 ]
Nektegayev, Ihor A. [4 ]
Matiychuk, Vasyl S. [2 ]
机构
[1] Danylo Halytsky Lviv Natl Med Univ, Dept Gen Bioinorgan Phys & Colloidal Chem, 69 Pekarska, UA-79010 Lvov, Ukraine
[2] Ivan Franko Natl Univ Lviv, Dept Organ Chem, 6 Kyryla & Mefodia, UA-79005 Lvov, Ukraine
[3] Danylo Halytsky Lviv Natl Med Univ, Dept Pharmaceut Chem FPGE, 69 Pekarska, UA-79010 Lvov, Ukraine
[4] Danylo Halytsky Lviv Natl Med Univ, Dept Pharmacol, 69 Pekarska, UA-79010 Lvov, Ukraine
关键词
Organic synthesis; thiazolo [4,5-b]pyridin-2-ones; anti-inflammatory activity; antioxidant activity; molecular docking; NONSTEROIDAL ANTIINFLAMMATORY DRUGS; ARYLATION PRODUCTS; HETEROCYCLES; DESIGN; NSAIDS; QSAR;
D O I
10.17344/acsi.2019.5439
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The synthesis, anti-inflammatory and antioxidant properties of novel 5-hydroxy-7-methyL-3H-thiazolo [4,5-b]pyridin-2-one derivatives were discussed. Fused thiazolo [4,5-b]pyridin-2-ones were synthesized and modified at the N-3, C-5 and C-6 positions of the main core in order to obtain the compounds with a satisfactory pharmacological profile. The synthesized compounds were preselected via molecular docking for further testing of their anti-inflammatory activity in vitro. Evaluation of novel compounds over the carageenin induced rat paw edema revealed strong anti-inflammatory action of some compounds including (thiazolo [4,5-b]pyridin-3(2H)-yl) propanenitrile (5) and thiazolo [4,5-b]pyridin-3(2H)-yl) propanoic acid (6) even exceeding the standard - Ibuprofen. The antioxidant activity of the synthesized compounds was measured in vitro by the method of scavenging effect on 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals.
引用
收藏
页码:1035 / 1043
页数:9
相关论文
共 50 条
  • [1] Antioxidant properties of some novel derivatives thiazolo[4,5-b] pyridine
    Chaban, Taras
    Ogurtsov, Volodymyr
    Mahlovanyy, Anatoliy
    Sukhodolska, Natalia
    Chaban, Ihor
    Harkov, Stefan
    Matiychuk, Vasyl
    PHARMACIA, 2019, 66 (04) : 171 - 180
  • [2] SYNTHESIS AND BIOLOGICAL PROPERTIES OF IMIDAZO-[4,5-B]-PYRIDINE DERIVATIVES
    KUCZYNSKI, L
    MROZIKIEWICZ, A
    POREBA, K
    POLISH JOURNAL OF PHARMACOLOGY AND PHARMACY, 1982, 34 (04): : 229 - 238
  • [3] Novel iminocoumarin imidazo[4,5-b]pyridine derivatives: design, synthesis, and biological evaluation
    Pavlinac, Ida Bocek
    Starcevic, Kristina
    Persoons, Leentje
    Banjanac, Mihailo
    Radovanovic, Vedrana
    Daelemans, Dirk
    Hranjec, Marijana
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2024, 60 (1-2) : 75 - 82
  • [4] Novel iminocoumarin imidazo[4,5-b]pyridine derivatives: design, synthesis, and biological evaluation
    Ida Boček Pavlinac
    Kristina Starčević
    Leentje Persoons
    Mihailo Banjanac
    Vedrana Radovanović
    Dirk Daelemans
    Marijana Hranjec
    Chemistry of Heterocyclic Compounds, 2024, 60 : 75 - 82
  • [5] Synthesis, characterization, and biological target prediction of novel 1,3-dithiolo[4,5-b]quinoxaline and thiazolo[4,5-b]quinoxaline derivatives
    El-Gaby, Mohamed S. A.
    Ammar, Yousry A.
    Ismail, Mostafa A.
    Ragab, Ahmed
    Abusaif, Moustafa S.
    HETEROCYCLIC COMMUNICATIONS, 2023, 29 (01)
  • [6] Synthesis and Biological Activities of Novel 1H-Imidazo[4,5-b]pyridine Derivatives
    Jebamani, Jesurajan
    Praneshm, Shubha Jayachamarajapura
    Shivalingappa, Jayadev
    Narayanarao, Manjunatha
    Pasha, Mussuvir
    Pawar, Chandrakant
    CHEMISTRYSELECT, 2023, 8 (28):
  • [7] Solid-Phase Synthesis of Thiazolo[4,5-b]pyridine Derivatives Using Friedlander Reaction
    Lee, Taeho
    Lee, Doohyun
    Lee, Ill Young
    Gong, Young-Dae
    JOURNAL OF COMBINATORIAL CHEMISTRY, 2010, 12 (01): : 95 - 99
  • [8] Synthesis, biological evaluation, and molecular docking studies of thiazolo[4,5-b]pyridin-5-ones as antimicrobial agents
    Kartsev, Victor
    Geronikaki, Athina
    Lichitsky, Boris
    Komogortsev, Andrey
    Petrou, Anthi
    Ivanov, Marija
    Glamoclija, Jasmina
    Sokovic, Marina
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2022, 59 (09) : 1573 - 1590
  • [9] Synthesis of new imidazo[4,5-b]pyridine derivatives
    Bukowski, L
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2002, (07): : 937 - 944
  • [10] Synthesis of isoxazolo[4,5-b]pyridine derivatives (microreview)
    Nikol'skiy, Vladislav V.
    Starosotnikov, Alexey M.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2023, 59 (4-5) : 240 - 242